EP3440056A4 - Pd(ii)-catalyzed enantioselective beta-methylene c(sp3)-h bond activation - Google Patents

Pd(ii)-catalyzed enantioselective beta-methylene c(sp3)-h bond activation Download PDF

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Publication number
EP3440056A4
EP3440056A4 EP17770916.9A EP17770916A EP3440056A4 EP 3440056 A4 EP3440056 A4 EP 3440056A4 EP 17770916 A EP17770916 A EP 17770916A EP 3440056 A4 EP3440056 A4 EP 3440056A4
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EP
European Patent Office
Prior art keywords
methylene
beta
bond activation
catalyzed enantioselective
enantioselective
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17770916.9A
Other languages
German (de)
French (fr)
Other versions
EP3440056A2 (en
Inventor
Jin-Quan Yu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Scripps Research Institute
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Scripps Research Institute
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Filing date
Publication date
Application filed by Scripps Research Institute filed Critical Scripps Research Institute
Publication of EP3440056A2 publication Critical patent/EP3440056A2/en
Publication of EP3440056A4 publication Critical patent/EP3440056A4/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
    • B01J2531/002—Materials
    • B01J2531/004—Ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)
  • Quinoline Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP17770916.9A 2016-03-21 2017-03-20 Pd(ii)-catalyzed enantioselective beta-methylene c(sp3)-h bond activation Withdrawn EP3440056A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662311039P 2016-03-21 2016-03-21
US201762447217P 2017-01-17 2017-01-17
PCT/US2017/023229 WO2017165304A2 (en) 2016-03-21 2017-03-20 Pd(II)-CATALYZED ENANTIOSELECTIVE BETA-METHYLENE C(sp3)-H BOND ACTIVATION

Publications (2)

Publication Number Publication Date
EP3440056A2 EP3440056A2 (en) 2019-02-13
EP3440056A4 true EP3440056A4 (en) 2019-11-27

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP17770916.9A Withdrawn EP3440056A4 (en) 2016-03-21 2017-03-20 Pd(ii)-catalyzed enantioselective beta-methylene c(sp3)-h bond activation

Country Status (5)

Country Link
US (1) US11186563B2 (en)
EP (1) EP3440056A4 (en)
JP (1) JP2019512519A (en)
CN (1) CN109563045B (en)
WO (1) WO2017165304A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021523092A (en) * 2018-03-21 2021-09-02 ピラマル・ファーマ・リミテッドＰｉｒａｍａｌ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ Improved asymmetric synthesis of alpha- (diarylmethyl) alkylamines
US11021427B2 (en) 2018-04-19 2021-06-01 The Scripps Research Institute Pd(II)-catalyzed enantioselective C—H arylation of free carboxylic acids
JP2021195368A (en) * 2020-06-10 2021-12-27 アムジエン・インコーポレーテツド Cyclobutyl dihydroquinoline sulfonamide compounds
CN113278045A (en) * 2021-05-14 2021-08-20 浙江工业大学 Polypeptide C (sp) guided by natural amino acid3) Method for arylation or alkynylation modification of-H bond
CN113731506B (en) * 2021-09-28 2023-05-26 常州大学 Method for assisting palladium-catalyzed fatty aldehyde C-H arylation reaction by calix [4] arene amide compound
WO2024091806A1 (en) * 2022-10-27 2024-05-02 The Scripps Research Institute Intermolecular beta-methylene c-h arylation of free aliphatic acids

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010050445A1 (en) * 2008-10-27 2010-05-06 武田薬品工業株式会社 Bicyclic compound
EP2397482A1 (en) * 2010-06-15 2011-12-21 Almirall, S.A. Heteroaryl imidazolone derivatives as jak inhibitors
CN102702218B (en) * 2011-03-26 2014-11-05 中国科学院上海有机化学研究所 Bis-oxazoline ligand compound containing chiral spirocyclic skeleton structure and preparation method and application thereof
CA2853876A1 (en) * 2011-11-02 2013-05-10 Bayer Intellectual Property Gmbh Compounds with nematicidal activity
US8980934B2 (en) * 2012-06-22 2015-03-17 University Health Network Kinase inhibitors and method of treating cancer with same

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
MASAYUKI WASA ET AL: "Ligand-Enabled Methylene C(sp 3 )-H Bond Activation with a Pd(II) Catalyst", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 45, 5 November 2012 (2012-11-05), US, pages 18570 - 18572, XP055632713, ISSN: 0002-7863, DOI: 10.1021/ja309325e *
QING-FENG WU ET AL: "formation of alpha-chiral centers", 3 February 2017 (2017-02-03), XP055632421, Retrieved from the Internet <URL:https://science.sciencemag.org/content/355/6324/499.full.pdf> [retrieved on 20191015] *
STAS MONIKA ET AL: "Conformational properties of oxazoline-amino acids", JOURNAL OF MOLECULAR STRUCTURE, ELSEVIER, AMSTERDAM, NL, vol. 1109, 6 January 2016 (2016-01-06), pages 192 - 200, XP029399869, ISSN: 0022-2860, DOI: 10.1016/J.MOLSTRUC.2016.01.001 *

Also Published As

Publication number Publication date
CN109563045A (en) 2019-04-02
CN109563045B (en) 2022-08-23
EP3440056A2 (en) 2019-02-13
US20190315710A1 (en) 2019-10-17
US11186563B2 (en) 2021-11-30
WO2017165304A2 (en) 2017-09-28
JP2019512519A (en) 2019-05-16
WO2017165304A3 (en) 2017-11-09

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